| Trophy | How to unlock
|
|---|
| 24 Karat | Finish the Gold Rush storyline.
|
| Alpha Male | Fight off a wolf attack.
|
| Bridger to Nowhere | Arrive at Jim Bridger's Trading Post.
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| Careful Driver | Complete a segment of the trail without hitting any obstacles.
|
| Classic Complaint | Have one of your passengers catch dysentery and don't administer medicine for it.
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| First Time Through | Get to Oregon for the first time.
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| Full House | Get to the end of the trail without losing any family members.
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| Have Gun, Will Shoot | Kill your first animal.
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| Hypochondriac | Use medicine on one of your sick passengers.
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| Journeyman | Score more than 120,000 points in a chapter.
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| Left Behind | Hunt for more than 150 pounds of food in one day.
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| Lickety Split | Arrive in Oregon with at least 45 days remaining.
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| Love Conquers All | Finish the Family Affair storyline.
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| Master Fisherman | Catch 60 pounds of fish in one day.
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| Piano Man | Bring the piano as your heirloom and complete the journey to Oregon.
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| Reel Talent | Catch your first fish.
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| Third Wheel | Break and replace two wagon wheels in one segment of the trail.
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| Trail Master | Score more than 150,000 points in a chapter.
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| Triple Threat | Finish the Three Brave Brothers storyline.
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| Uncivil War | Finish the Stuck in the Middle storyline.
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| Victimized | Get robbed 10 total times in one trip down the trail.
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| Walla Walla | Arrive at Walla Walla, Washington.
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